Cylk Cozart (Hank Farley) plays a college football player in this episode, when in actuality he was 36 years old at the time the episode aired.
When Will & Carlton are in the backyard, Will says "It's like I could see myself being stupid, but I couldn't do nothin' about it... That must be what Chevy Chase felt like." Will is referring to the much maligned and short-lived The Chevy Chase Show (1993), a late night talk show hosted by Chevy Chase that lasted less than 3 weeks before being canceled in September 1993.
When Will is at the party bragging about playing football for Notre Dame he says "Of course, when Hollywood got a hold of my story they made it a white dude." The movie he's talking about is Rudy (1993).
In one part, Judith (played by Robin Quivers), mentions working with a best selling author. This is clearly a reference to her long time partner, Howard Stern.